An efficient synthesis of the N-methylwelwistatin tetracyclic core in only two steps from Kornfeld's ketone is described, whose key transformation involves the generation of a fused bicyclo[4.3.1]decane ring system through a one-pot sequence comprising a Michael-intramolecular aldolization anionic domino process and a DBU-promoted hydrolysis of the N-pivaloyl protecting group. Besides providing...

The title compound, C(24)H(21)N(3)O, was prepared by the reaction of (Z)-2-(1H-indol-3-ylmethyl-ene)-1-aza-bicyclo-[2.2.2]octan-3-one with α-bromo-p-toluonitrile, under phase-transfer catalytic (PTC) conditions using triethyl-benzyl-ammonium chloride and 50% w/v aqueous NaOH solution in dichloro-methane. The crystal structure indicates the presence of a double bond with Z geometry connecting th...

In the title compound, C(14)H(20)N(2)O(2)S, the sulfonamide O atoms lie to one side of the benzene ring and the amino-bicyclo-hepta-nyl to the other side [C(ar)-S-N-C torsion angle = -57.93 (11)°; ar = aromatic]. An intra-molecular N-H⋯N hydrogen bond is formed. In the crystal, a supra-molecular chain is formed along the b axis via N-H⋯O and N-H⋯N hydrogen bonds.

The asymmetric unit of the title compound (C6H14N2)[CdCl4]·H2O contained one 1,4-di-aza-bicyclo-[2.2.2]octane dication, a tetrahedral CdCl4 (2-) anion and a lattice water mol-ecule. In the crystal, the solvate water mol-ecule inter-acts with the cationic and anionic species via N-H⋯O and O-H⋯Cl [O⋯Cl = 3.289 (7) Å] hydrogen-bond inter-actions, respectively, leading to a layered supramolecular s...

Attempted oxidation of a TADDOL-derived bisthioacetate resulted in a rather unexpected and remarkable cyclization and deprotection reaction, giving a thiolane-1, 1-dioxide as the main product. Systematic in situ ESI-HRMS studies revealed a bicyclic, highly acid labile key intermediate of this reaction. Supported by force field calculations, the high sensitivity of this intermediate was judged t...

The crystal structures of the new compounds spiro[cyclohexane-1,3’-indol]-2’(1’H)-one (1), (rel-1R,2S)-spiro[bicyclo[2.2.1] heptane-2,3’-indol]-2’(1’H)-one (2) and spiro[indole-3,2’-tricyclo[3.3.1.1]decan]-2(1H)-one (3) have been determined by low temperature single crystal X-ray diffraction. The effects of substitution on the hydrogen bonding pattern is compared between all three compounds.

prenylated indole alkaloids that are secondary metabolites produced by Penicillium sp. and Aspergillus sp. fungi. This review will cover both the biosynthesis as well as the chemical synthesis of this family of natural products. Particular emphasis will be placed on the provocative hypothesis that the core bicyclo[2.2.2]diazaoctan ring system, which is common to this entire family, is formed by...

The title compound, C(16)H(19)NO, was synthesized under solvent-free conditions by reaction of 7-oxa-bicyclo-[4.1.0]heptane and naphthalen-1-amine in the presence of Ca(CF(3)COO)(2) as catalyst. The cyclo-hexane ring adopts a chair conformation. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds and C-H⋯π inter-actions into chains parallel to the c axis.